Manager, Major Gifts

Outward Bound Canada is committed to inclusion and strives to have broad representation that reflects the diversity of Canada. We encourage applications from candidates who identify as Black, Indigenous, People of Colour or People of the Global Majority, members of the 2SLGBTQIA+ community, and all other equity-deserving groups.


Outward Bound Canada is seeking an experienced fundraising professional with a strong track record of securing and managing five- and six-figure donations. The Manager, Major Gifts will be responsible for leading the cultivation, solicitation, and stewardship of OBC’s major gifts portfolio (donations of $25,000+). Reporting to the Head of Development and Engagement, the Manager will oversee a portfolio of 75-125 donors and prospects while working collaboratively with other members of the Development Team and the Fundraising Cabinet. The Manager will identify opportunities to welcome new donors to OBC, while also strengthening existing relationships, leading to greater engagement with OBC’s mission, increased giving levels, and multi-year pledges. In addition, the Manager will support OBC’s legacy giving campaign and supervision of those tasked with managing annual and special events.


Location: Toronto, Ontario
Salary: $65,000-$80,000 annually
Benefits: Comprehensive benefits package and Employee Assistance Plan
Term: Full Time
Supervisor: Head of Development and Engagement
Application Deadline: November 24, 2022
Anticipated Start Date: January 2023


  • Develop and maintain an in-depth knowledge of OBC programs and funding priorities.
  • Provide strategic oversight of the major gift portfolio (donations of $25,000+), building relationships with individuals and organizations capable of this level of support.
  • Establish an effective stewardship program for various levels of major gifts, which includes appropriate reporting and engagement activities.
  • Establish goals to move donors up the giving cycle and solicit multi-year pledges.
  • Work collaboratively with the rest of the Development Team to ensure the successful execution of fundraising and stewardship strategies and programs to maximize revenue.
  • Maintain a challenging but realistic portfolio of major gift prospects to cultivate, solicit, and steward, both personally and in tandem with senior staff and volunteers.
  • Develop the organization’s legacy giving program and promote with key stakeholders.
  • Support the Head of Development and Engagement, Executive Director (ED), Board members, Fundraising Cabinet, and volunteer committees in coordinating and implementing national fundraising efforts.
  • Design and execute annual and special events, including third-party events and community opportunities that raise funds in support of Outward Bound Canada and increase engagement.
  • Ensure systems are in place to provide acknowledgment, recognition, reporting, and effective communication for donors and prospects.
  • Organize, manage and track fundraising activities and information, ensuring donor activity is maintained in the database.
  • Utilize prospect research tools to identify and qualify potential major gift donors as well as the cultivation and solicitation of prospects to meet revenue targets.
  • Assist in the creation of donor communications and fundraising materials in collaboration with the Philanthropy and Marketing teams.
  • Represent OBC at fundraising events and on fundraising projects as required.
  • Provide relevant and engaging reporting programs for the major donor program.
  • Other duties as assigned.


OBC recognizes relevant skills and knowledge can be gained through volunteer and life experiences as well as professional and educational backgrounds. Please outline in a brief cover letter how you have gained the following experiences, and how you would apply them to this role:


  • University degree or relevant post-secondary education.
  • 5-7 years of experience in fundraising, major gifts, and/or gift planning experience for a registered charity.
  • Experience working with senior volunteers and advancement staff.
  • Must have excellent prospecting skills and a proven ability to uncover leads from databases and other sources.
  • Proven track record in major gift cultivation and solicitation activities.
  • Demonstrated awareness of the donor relationship cycle (identification, cultivation, solicitation, stewardship); principles of moves management, and a solid understanding of how major gift activities relate and connect to other major gift areas within development such as events, stewardship, research, annual and planned giving.
  • Flexible and adaptable; able to work both independently and as part of a team; proven ability to set priorities; work with minimal supervision and meet deadlines.
  • Proficiency with databases, NetSuite, GSuite and a high degree of comfort with a donor database for tracking prospect activity.
  • Excellent interpersonal skills and a positive attitude to work effectively and collaboratively with a variety of stakeholders such as volunteers, donors, and alumni.
  • Superior organizational, administrative, analytical, verbal, and written communication skills.
  • Exceptional attention to detail, ability to develop and execute complex plans and manage multiple priorities and deadlines.
  • Professional presence, sound judgment, diplomacy, and tact. Ability to maintain confidentiality and work with sensitive information.
  • The position requires a police background check, including a Vulnerable Sector Check.
  • Evening and weekend work will be required from time to time.
  • Fully vaccinated against Covid-19
  • Clear Vulnerable Sector Check
  • Personal commitment to equity and inclusion in the outdoors
  • Understanding of how systems of oppression take shape in workplaces and a desire to shift the balance of power and privilege to center underrepresented voices
  • High level of cross-cultural competence, in recognition, that Outward Bound Canada works with students and partners from a diversity of communities and backgrounds
  • Passionate about the Outward Bound Canada mission, an interest in outdoor pursuits, and a desire to help get young people outdoors for transformative experiences


  • Certificate in Fundraising Management or Fundraising Executive designation (CFRE) an asset.
  • Working knowledge of a CRM database (e.g., NetSuite, SalesForce, Raiser’s Edge, etc.)

At Outward Bound Canada we believe that communities that have been historically underrepresented in outdoor recreation must be centered in the work we do. Therefore, we strongly encourage applications from people who will increase representation, and invite applicants to outline how they will contribute to this in their application.

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